(1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene

Base Information

• Chemical Name: (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene
• CAS No.: 1260224-16-5
• Molecular Formula: C₂₀H₂₇N
• Molecular Weight: 281.441

Synonyms:(1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene

Chemical Property of (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene

Chemical Property:

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Technology Process of (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene

There total 7 articles about (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.6%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1S,3R,4aS,8aR)-N-benzyl-3,6-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-amine (1260224-15-4) → (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene (1260224-16-5)

Guidance literature:

With silica gel; In water; acetic acid; at 60 ℃; for 16h;

DOI:10.1021/ja312065m

Reference yield:

(3'R,4a'S,8a'R)-3',6'-dimethyl-3',4',4a',5',8',8a'-hexahydro-2'H-spiro[[1,3]-dioxolane-2,1'-naphthalene] (1260224-14-3) → (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene (1260224-16-5)

Guidance literature:

Multi-step reaction with 3 steps

1: acetone / 2.5 h / 20 °C

2: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 50 °C

3: acetic acid / water / 16 h / 60 °C

With sodium tris(acetoxy)borohydride; acetic acid; acetone; In water; 1,2-dichloro-ethane; 3: Aza-Prins reaction;

DOI:10.1021/ja109516f

Reference yield:

(R)-5-methyl-cyclohex-2-enone (54307-74-3,15466-88-3) → (1S,4S,6R,8S,9R)-3-benzyl-6,11-dimethyl-3-azatricyclo[6.2.2.0(4,9)]dodec-11-ene (1260224-16-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

1.2: 25 h / -78 °C / Inert atmosphere

2.1: acetone / 2.5 h / 20 °C

3.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 12 h / 50 °C

4.1: acetic acid / water / 16 h / 60 °C

With trimethylsilyl trifluoromethanesulfonate; sodium tris(acetoxy)borohydride; acetic acid; acetone; In dichloromethane; water; 1,2-dichloro-ethane; 1.2: Diels-Alder reaction / 4.1: Aza-Prins reaction;

DOI:10.1021/ja109516f

upstream raw materials:

formaldehyd

(1S,3R,4aS,8aR)-N-benzyl-3,6-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalen-1-amine

(3'R,4a'S,8a'R)-3',6'-dimethyl-3',4',4a',5',8',8a'-hexahydro-2'H-spiro[[1,3]-dioxolane-2,1'-naphthalene]

(R)-5-methyl-cyclohex-2-enone

Downstream raw materials:

C₂₁H₂₇Br₂N

(1S,3R,4S,6R,8R,9R)-13-bromo-6,12-dimethyl-10-azatetracyclo[7.2.2.0^3,8.0^4,10]tridec-12-ene

C₂₁H₂₆BrN

(1S,3R,4S,6R,8R,9R)-6,12-dimethyl-13-(phenylthio)-10-azatetracyclo[7.2.2.0^3,8.0^4,10]tridec-12-ene

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